Methyl iodide → HCID 54333640, compound

HRID 2290128Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[CH:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].IC.CN(C)[C:38](=O)[CH3:39]>>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:38][CH3:39])[C:12]2[CH:13]=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:15]3[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=3[CH:22]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 31374Dimethylacetamide

HCID 54068193HCID 54068193, compound2×

Product 1

HCID 54333640HCID 54333640, compoundYield 56%

Procedure

Following general procedure G and using 4-[(7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 18, 0.15 g, 0.41 mmol), potassium carbonate (1.65 g, 12 mmol) and iodomethane (0.94 g, 6 mmol) in 5 mL of anhydrous N,N-dimethylacetamide, the title compound (0.090 g, 56%) was obtained as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.85 (d, 2H, J=8.9 Hz), 6.87 (d, 1H, J=2.2 Hz), 6.77 (d, 1H, J=2.2 Hz), 6.57 (d, 2H, J=9.1 Hz), 4.29 (q, 2H, J=7.1 Hz), 4.28 (s, 2H), 3.74 (q, 2H, J=7.0 Hz), 1.36 (t, 3H, J=7.1 Hz), 1.36 (s, 9H), 1.33(s, 6H), 1.26 (t, 3H, J=7.1 Hz)).

Sources & evidence

ORD record: ord-26394582cf6a4f198fdf95cf35ab7183
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093838

Reaction notes

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